Every year, I get a few requests from young high schoolers or college kids, who have been given an assignment to interview someone “famous” and bring the evidence back to class to share.

I recently sent an e-mail to the son of an old friend who had contacted me, and I figured, “What the heck – share this...”

Here are his questions and my answers:

How would you define success?

Success is fulfillment (or, at least, always aiming towards fulfillment – intention, if not necessarily successful outcomes all the time): for me, always – happiness and security for the people I love. A comfortable self-image and self-awareness as one feels/considers the orbit of the seven circles that run through their heart and soul:

1.

Family and friends – love and friendship.

2.

Community – virtuous social behavior (seven virtues: boil it down to Golden Rule and acting in good faith).

3, 4 and 5.

The 3 levels of government that you get to vote at [municipal, provincial, federal] – political, social and cultural participation: being a conscientious citizen.

6.

Citizen of the planet earth. (Leave the campsite the way you found it? Better than you found it?)

7.

Tiny speck in the infinite universe. (God? Mother Nature? Why are we here? Why are you here? What will you do with your short little dance on this little blue ball that circles the sun?)

What is your occupation? How long have you been doing what you’re doing? Have you had any other jobs?

Singer/songwriter /musician/guitarist. Started singing in the choir as an 8-year-old. Started writing songs when I was about 11. Got very serious about professional guitar playing when I was 17, and joined the musician’s union, playing weddings, bar mitzvahs, gigging weekends in a country band, etc.

I had part-time jobs as a drugstore delivery boy, a pin-jam-clearer in a bowling alley, a vacuum operator in a car wash, a drop-in center gym instructor, a camp counselor, a public school teaching assistant and a music teacher [both privately and in summer music schools].

Did you have any special training to get where you are now? If so, what kind?

I’ve only got a Ph.D. from the School of Hard Knocks.

I spent one semester in the music program at Humber College, but that experience only reinforced my suspicion that I was not an academic, but a performer. Ironically, I am now on the faculty in that program, and have been awarded an honorary diploma. I teach music business, songwriting and consult on the graduate year recording program (directed studies).

What changes have you experienced throughout your working life?

Far too many to list. A career in show business is all about constant change: the digital age has only increased the rate of change to the speed of light [the rate of bits and bytes flowing through fiber optic cable, and bouncing off satellites]. You have to be light on your feet, keeping centered and balanced. It’s a tricky challenge, and never completely successful. But “success” is often measured by simple survival. (Maybe that should have been part of the answer to question #1. Change, morph, adapt.) The biggest changes happen to the business around me, and therefore my role and my image and my work must adapt to those changes. But the biggest change inside me is to try and maintain my own sense of purpose, and my integrity and dignity, even as I get older and my skill set, um, matures – and the business swirling around me creates its own pressures and compromises. This is delicate and gentle diplomacy, these arts and crafts: to be able to compromise, collaborate and cooperate, without sacrificing any of one’s own sense of dignity and integrity. Sounds easier than the way it plays out. One requires a strong personal moral compass, combined with great humility in the face of the infinite challenge of music-making.

How did you cope with these changes?

The best that I can. I make a whole bunch of mistakes. And I get knocked down fairly easily. But I’m also fairly predictable: when I get knocked down, I get back up on my feet again, and try to find my center of balance. Long ago, I decided I could never win the war: it was all about trying to fly under the radar, and fight a kind of guerilla campaign, and just win the minor, um, engagements, here and there – try to pick my own moments, and remain the master of my own destiny in a small, humble way.

The single constant I remind myself about; I see the same face in the mirror every morning. It’s my own head that I have to reconcile with, when it hits the pillow every night. If I want to like that guy I see, and sleep well with him, I’d better make choices that keep him satisfied.

You have to know yourself. I get myself in trouble when I lose sight of who I am, and forget who I am, and what I’m made of. This is not heroic talk, by any stretch. It is, however, about a sense of integrity.

How did these changes influence your career path?

I hitched my wagon to rising stars and partners early on, and learned a great deal, and had some very lucky success from some right-thing-at-the-right-time opportunities. I’ve also made some career choices that were extremely difficult, when it came to “integrity,” and some things that you go through are also very much about how time plays into the equation. Over the years, I eventually downsized to an indie, self-employed, artist who decided that – as it says in my bio – a unique artist can still keep going strong if the career path is based on being a loyal friend to one’s gifts, instead of being a slave to fashion (with luggage to match). The less luggage I carry along, the easier it is to handle, with my aging capabilities. This may just be a fancy way of saying – keep it simple, stupid.

A sense of humour is also critical, I truly believe. You have to be able to laugh at yourself. And also at the slings and arrows of outrageous fortune.

Are you happy doing what you are doing now?

Yes. It is satisfying. I still consider myself very lucky to get the opportunities that come my way. I still make a lot of mistakes, but I find that audiences and fans are very gracious, forgiving and willing to cut me plenty of slack and give me latitude, as long as I show my concerns and pay service to their expectations of me. (There is no point in denying a hall-of-fame lifetime career of luggage: I just don’t want to get buried under it, and lose my sense of direction.)

What have you learned from the variety of experiences you have had and roles you have played?

Not to get too far up or down, not to swing too far left or right: all that talk about balance and even keel makes good common sense. I always say to students – don’t let your own ego get out in front of the music: let the music lead you and tell you what it needs. Humility in the face of the infinite challenge: it keeps the focus in the right place. It’s not about rich and famous. It’s about the work. It’s about enjoying and loving the process. I love the chance to make music. I may not be the world’s greatest, and I may not even be having a great night, but if I always show people that I love that opportunity, and I remain dedicated to the work, with good faith, it seems to work out more often than not.

Paul McCartney was the eternal optimist in The Beatles, and a song like “We Can Work it Out” resonates because I think he believes it’s true. Whether it was/is or not, he was being honest. Honest work is cleansing – healthy.

What advice would you give to a grade 10 student who is beginning to plan for their future?

Plan for a future that will change even more rapidly than it does now. It’s not about fearing change: it’s about how you embrace it and integrate it into your own vision and mission. Know your limitations, and be realistic. Don’t keep disappointing yourself by setting short-term goals that you can’t achieve. Set short-term goals that you can accomplish, and make yourself into a winner: someone who can believe in yourself.

And at the same time, plan for a future where you can put your heart and soul into the work you do, whether you are a poet or a plumber, a kindergarten teacher or a Ph.D. There is honour and dignity – integrity – in every choice you get the chance to make, so take the time to ask yourself – Who is the best me that I can imagine? And what choice would that “best me” make?

Make those choices consistently, and you will become the best you that you can be.